(5aR,8aR,9R)-5,8-Dioxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester

Base Information

• Chemical Name: (5aR,8aR,9R)-5,8-Dioxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester
• CAS No.: 620116-57-6
• Molecular Formula: C₂₆H₂₄O₁₀
• Molecular Weight: 496.471
• Mol file: 620116-57-6.mol

Synonyms:(5aR,8aR,9R)-5,8-Dioxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester

Chemical Property of (5aR,8aR,9R)-5,8-Dioxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5aR,8aR,9R)-5,8-Dioxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester

There total 7 articles about (5aR,8aR,9R)-5,8-Dioxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(5aR,8aR,9R)-5-Hydroxy-8-oxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester → (5aR,8aR,9R)-5,8-Dioxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester (620116-57-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 25 ℃; for 0.5h;

DOI:10.1021/ja0376588

Reference yield:

4-isopropyl-2-naphtho[2,3-d][1,3]dioxol-6-yl-4,5-dihydro-oxazole → (5aR,8aR,9R)-5,8-Dioxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester (620116-57-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: tetrahydrofuran / 3 h / -78 °C

1.2: tetrahydrofuran / -78 - 25 °C

1.3: 202.6 mg / aq. KHCO₃; aq. K₂CO₃ / methanol / 55 h / 25 °C

2.1: MeOTf / CH₂Cl₂ / 2 h / 25 °C

2.2: NaBH₄ / tetrahydrofuran; methanol / 0.5 h / 25 °C

2.3: 100 percent / (CO₂H)2*H₂O / tetrahydrofuran; H₂O / 16 h / 25 °C

3.1: 79 percent / Bu₃SnH; SiO₂ / toluene / 10 h / 80 °C

4.1: 99 percent / pyridine / CH₂Cl₂ / 2 h / 25 °C

5.1: 40 percent / tris(trimethylsilyl)silane; AIBN / benzene / 14 h / 80 °C

6.1: BF₃*2AcOH / CH₂Cl₂ / 27 h / 50 °C

6.2: m-CPBA; KF / dimethylformamide / 1 h / 25 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 25 °C

With pyridine; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; tri-n-butyl-tin hydride; boron trifluoride diacetate; silica gel; Dess-Martin periodane; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; toluene; benzene; 6.2: Fleming-Tamao oxidation;

DOI:10.1021/ja0376588

Reference yield:

(5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-formyl-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester (620116-53-2) → (5aR,8aR,9R)-5,8-Dioxo-9-(3,4,5-trimethoxy-phenyl)-5,8,8a,9-tetrahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5a-carboxylic acid allyl ester (620116-57-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 79 percent / Bu₃SnH; SiO₂ / toluene / 10 h / 80 °C

2.1: 99 percent / pyridine / CH₂Cl₂ / 2 h / 25 °C

3.1: 40 percent / tris(trimethylsilyl)silane; AIBN / benzene / 14 h / 80 °C

4.1: BF₃*2AcOH / CH₂Cl₂ / 27 h / 50 °C

4.2: m-CPBA; KF / dimethylformamide / 1 h / 25 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 25 °C

With pyridine; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; tri-n-butyl-tin hydride; boron trifluoride diacetate; silica gel; Dess-Martin periodane; In dichloromethane; toluene; benzene; 4.2: Fleming-Tamao oxidation;

DOI:10.1021/ja0376588

upstream raw materials:

(5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-formyl-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester

(5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-hydroxymethyl-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester

(5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-((S)-4-isopropyl-4,5-dihydro-oxazol-2-yl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester

(5S,6S)-5-(Dimethyl-phenyl-silanyl)-6-(3,4,5-trimethoxy-phenoxythiocarbonyloxymethyl)-5,6-dihydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid allyl ester

Downstream raw materials:

(1α,2α,3α)-podophyllotoxin

Refernces